Tom Warshaw (DAVID DUCHOVNY) is an American artist living in contemporary Paris with his wife, Coralie (MAGALI AMADEI) and son, Odell (HAROLD CARTIER), who's just turning 13. That milestone brings back both good and bad memories for Tom and he decides to tell his family about the pivotal events of his past that changed him forever.
The year is 1973 and Tommy (ANTON YELCHIN) lives in New York's Greenwich Village with his mom (TÉA LEONI). She hasn't been the same since the death of Tommy's father and is now overly protective of him when not depressed. He goes to a Catholic school run by Rev. Duncan (FRANK LANGELLA) where he likes to hang out with the middle-aged and mentally challenged assistant custodian, Pappass (ROBIN WILLIAMS). The two are not only friends, but also coworkers employed by Simone (OLGA SOSNOVSKA) delivering meats from the corner butcher shop to various nearby homes.
Their friendship has become a bit strained of recent, however, since Pappas is jealous of Tommy's interest in girls, especially Melissa (ZELDA WILLIAMS). Unsure of how to act around her, Tommy finds an unlikely mentor in Lady Bernadette (ERYKAH BADU), a prostitute imprisoned in the Village's House of Detention. Only able to see him via a mirror she holds out the window, Bernadette gives Tommy all sorts of advice about his life and relationship with others in it. When an unexpected tragedy then strikes, Tommy must figure out what to do next, a decision that will affect the rest of his life.